NZ199022A - Preparation of 5,6,7,7a-tetrahydro-4h-thieno (3,2,-c) pyridin-2-one derivatives - Google Patents
Preparation of 5,6,7,7a-tetrahydro-4h-thieno (3,2,-c) pyridin-2-one derivativesInfo
- Publication number
- NZ199022A NZ199022A NZ199022A NZ19902281A NZ199022A NZ 199022 A NZ199022 A NZ 199022A NZ 199022 A NZ199022 A NZ 199022A NZ 19902281 A NZ19902281 A NZ 19902281A NZ 199022 A NZ199022 A NZ 199022A
- Authority
- NZ
- New Zealand
- Prior art keywords
- process according
- tetrahydro
- thieno
- pyridin
- acid
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
New Zealand Paient Spedficaiion for Paient Number 1 99022
K99022
Priority Date(s); .
Ccmplets Specification Filed: $P. './/.$ Ctess: Q9J.V. A..........
,;..0.P.HARJ9S4
\Ql5Q>.
| Publication Date; j r? n, Jcxr^rl IMo
• aaaicig t e ,«5s pf®. m V ® t? «?•
li fa 7*>3 fe fi ■'■■.•» ft u".f- i-.jia
1II ^ m WI P ^
:? >\
NOV 1501 j
Patents Fonn No. 5
PATENTS ACT 1953
Number Dated
COMPLETE SPECIFICATION
PROCESS FOR THE PREPARATION OF 5,6,6,7a-tetrahydro-4H-thieno (3,2-c)pyridin-2-one derivatives
&We SANOFI a French Company of 40 Avenue George V, 75008 Paris, France do hereby declare the invention for which Jt/we pray that a Patent may be granted to wk/us, and the method by which it is to be performed, to be particularly described in and by the following statement:
2
199022
The present invention is concerned with a novel process for the preparation of 5,6,7,7a-tetrahydro-4H thieno (3,2-c)pyridin-2-one derivatives.
The 5,6,7,7a-tetrahydro-4H-thieno (3,2-c)-pyridin-2-one derivatives with which the present invention is concerned are compounds of the general in which R is a hydrogen atom or a phenyl radical optionally substituted by at least one halogen atom,
lower alkyl radical, lower alkoxy radical, nitro group, carboxy group, alkoxycarbonyl radical or cyano group; R' is a hydrogen atom or a lower alkyl radical and n is 0,1,2,3, or 4; as well as the addition salts thereof with mineral and organic acids.
In this specification the qualifying term "lower" is intended to mean "having from one to four atoms in the carbon chain " so that, for example, "lower" alkyl means alkyl having from one to four atoms in the carbon chain.
These compounds (I) have platelet anti-aggregant properties and anti-thrombotic properties and are the subject matter of our New Zealand Patent Application No. 199021 filed simultaneously.
Furthermore they are also included in a general formula given in New Zealand Patent Specification No. 181687 and
British Patent Specification No. 1,445,524 in the following tautomeric form:-
formula: -
(I)
/
199022
in which R, R' and n have the same meanings as above.
However, none of the compounds (I) is specifically described therein.
According to the present invention, there is provided a process for the preparation of compounds of general formula (I), wherein a) a compound of the general formula:
in which R, R1 and n have the same meanings as above, is treated with a solution of hydrogen peroxide in a mixture of acetic acid and hydrobromic acid to give a brominated derivative of the general formula:-
in which R, R' and n have the same meanings as above; b) the brominated derivative (III) is converted into an organo-magnesium compound in an inert anhydrous solvent, this organo-magnesium compound then being condensed with tert.-butyl perbenzoate to give a compound of the general formula:-
(II)
(III)
(IV)
CH
3
199022
in which R, R* and n have the same meanings as above; and c) the compound (IV) is heated to a temperature of from 80 to 180°C. in the presence of a mineral or organic acid to give the desired derivative of general formula (I).
The mixture of acetic acid and hydrobromic acid used in step a) is preferably within the limits of 50/50 to 80/20.
The hydrobromic acid used in step a) is preferably 48% hydrobromic acid and the acetic acid used is preferably pure.
The hydrogen peroxide solution employed in step a) is preferably an alcoholic solution of hydrogen peroxide,
such as a methanolic solution of 30% hydrogen peroxide.
In step b), the inert solvent, such as tetrahydro-furan, may be used not only for the preparation of the organo-magnesium compound but also for the subsequent condensation of this organo-magnesium compound with tert.-butyl perbenzoate.
The organo-magnesium compound is prepared in conventional manner, for example with the use of metallic magnesium and an alkyl halide, such as isopropyl bromide, in an anhydrous medium.
It is not necessary to isolate the organo-magnesium compound from the reaction mixture prior to condensation thereof with tert.-butyl perbenzoate.
"Kl • " - - - - --
199022
In step c)# a mineral or organic acid is added, an example of a preferred acid being j>-toluenesulphonic acid.
The process according to the present invention may be represented by the following reaction scheme:
^ (CHR* )^R ^ ^(CHR')^-R
LV0 jX)
(II) (III)
2) CcHcCO.O.O-t.C.Hn H^C-CO 6 5 — 4 y J
(chr') —r
1) Mg CH, l~, if N~ n H+
(I)
ch3 (iv)
The starting materials of general formula (ii) may be prepared by means of the processes described in the literature, for example, by means of the processes described in the above-mentioned New Zealand Patent Specification No.' 181687 and British Patent Specification No. 1,445,524.
The following Examples are given for the purpose of illustrating the present invention:-Example 1.
-(2-Chlorobenzyl)-5,6,7,7a-tetrahydro-4H-thieno-(3,2-c)-pyridin-2-one. Formula (i); R = 2-Cl.CgH^; R' = H; n = 1; Derivative No.l.
1 o q p. 9 o f / / U l! l
A mixture of 3 cc. 30% hydrogen peroxide and 10 cc. methanol is added dropwise to a solution, cooled to 0°C.,
of 2.63 g. 5-(2-chlorobenzyl)-4,5,6,7-tetrahydro-(3,2-c)-pyridine in 10 cc. acetic acid and 6 cc. 48% hydrobromic acid.
When the addition is finished, the reaction mixture is stirred at ambient temperature for 10 minutes, then a solution of sodium hydrosulphite is added thereto,
followed by a solution of sodium carbonate, whereafter the reaction mixture is extracted with a mixture of benzene and chloroform. The organic extracts are washed with water, dried with anhydrous sodium sulphate and filtered. A solution of gaseous hydrogen chloride in methanol is added to the filtrate, followed by concentration in a vacuum. Recrystallisation of the solid residue obtained from ethanol gives 2.0 g. of beige crystals in platelet form, this product being 2-bromo-5-(2-chlorobenzyl)-4,5,6,7-tetrahydro-thieno(3,2-c)-pyridine; m.p. with decomposition at about 180°C.
A mixture of 1.075 g. of the free base, 0.19 g. magnesium, 0.57 g. isopropyl bromide and 10 cc. tetra-hydrofuran is heated under reflux for 2 hours under an atmosphere of nitrogen. After cooling, 1.5 g. tert.-butyl perbenzoate is added thereto and the reaction mixture then stirred for 15 hours at ambient temperature and subsequently for 1 hour under reflux. The reaction mixture is poured into an aqueous solutic O,
A
"\
199022
of sodium citrate and sodium carbonate and then extracted with benzene. The organic extracts are washed with water, dried with anhydrous sodium sulphate and concentrated under reduced pressure. The oily residue obtained is purified by chromatography on a column of silica, 0.25 g. of a yellow oil being obtained.
100 mg. of this compound and 100 rag. j>-toluene-sulphonic acid are heated to 150°C. for 9 minutes.
After rapid cooling, the reaction mixture is added to a mixture of 10 cc. 0.15M phosphate buffer (pH 5.5) and 20 cc. butanol. The organic phase is evaporated under reduced pressure. The residue obtained is purified by chromatography on a silica column to give 5-(2-chlorobenzyl)-5,6,7,7a-tetrahydro-4H-thieno(3,2-c)-pyridin-2-one; m.p. 73 - 74.5°C. (recrystallised from ethanol).
The corresponding oxalate melts at 168 - 170°C., after recrystallisation from ethanol; IR (KBr): V CO » 1660 cm~* (large).
The corresponding hydrochloride semihydrate,
after precipitation from acetone, melts with decomposition at about 180°C.
The base melts at 73 - 74.5°C., after recrystallisation from ethanol; NMR (CDCl^): 7.1-7.6 (ra,4H); 6.2 (s,lH); 4.2-4.7 (m,lH); 3.9 (s,2H)r 1.5-4.2 (m,6H). Example 2.
-Benzyl-5,6,7,7a-tetrahydro-4H-thieno(3.2-c)-pyridin-2-one.Formula (I); R = R* *= H; n = 1; Derivative No.2.
|99(D2?
This is prepared according to the method of Example 1,starting from 5-benzyl-4,5,6,7-tetrahydro-thieno(3,2-c)-pyridine. Maleate: beige crystals; m.p. 132 - 134°C., recrystallised from isopropanol; IR (KBr): v CO = 1680 cm"1. Base: NMR (CDC13): 7.25 (m,5H); 5.90 (s,lH); 3.60 (s,2H).
Example 3.
-(4-Chlorobenzvl)-5,6,7.7a-tetrahydro-4H-thieno(3.2-c)-pyridin-2-one. Formula (I); R = 4-Cl.CgH^r R' = H; n =s 1; Derivative No. 3
This is prepared according to the method of Example 1, starting from 5-(4-chlorobenzyl)-4,5,6,7-tetrahydro-thieno(3,2-cJpyridine. Maleate: beige crystals; m.p. 158 - 160°C., recrystallised from ethanol; IR (KBr): i) CO =» 1680 cm"1. Base: NMR (CDC13): 7.30 (ra,4H); 6.0 (s,lH); 3.50 (s,2H).
Example 4.
-(2-Methylbenzyl)-5,6.7.7a-tetrahydro-4H-thieno(3,2-c)-pyridin-2-one. Formula (I); R » 2-H^C.CgH^; R* ■ H; n = 1; Derivative No.4.
This is prepared according to the method of Example 1, starting from 5-(2-methylbenzyl)-4,5,6,7-tetrahydro-thieno(3,2-c)-pyridine. Oxalate: beige crystals, m.p. 195 - 197°C., recrystallised from methanol; IR (KBr): V CO = 1690 cm"1. Base: NMR (CDC13): 7.lO(s,4H); 5.90 (s,lH); 3.55 (s,2H); 2.30 (s,3H).
i99022
9
Example 5.
-fl-(2-Chlorophenyl)-ethyl]-5.6,7,7a-tetrahydro-4H-thieno(3.2-c)-pyridin-2-one. Formula (I); R = 2-Cl.CgH^r R' = CH3* n = 1; Derivative No.5.
This is prepared according to the method of Example 1, starting from 5-[l-(2-chlorophenyl)]-4,5,6,7-tetrahydrothieno(3,2-c)-pyridine. Hydrochloride: yellow crystals; m.p. 140 - 142°C.; IR (KBr): V CO = 1690 cm-1; Base: NMR (CDC13): 7.30 (m,4H); 6.05 and 5.95 (2s,lH); two diastereoisomers.
Example 6.
-f1-(2-Chlorophenyl)-propyl1-5,6.7,7a-tetrahydro- 4H-thieno 3.2-c)-pyridin-2-one. Formula (I); R = 2 Cl-C^H^; R* = C2H(jT n = 1; Derivative No. 6.
This is prepared according to the method of Example 1, starting from 5-[l-(2-chlorophenyl)]-4,5,6,7-tetrahydrothieno(3,2-c)-pyridine. Hydrochloride: beige crystals; m.p. 124 - 126°C.; IR (KBr): \) CO = 1690 cm-1. Base: NMR (CDC13): 7.30 (m,4H); 6.05 and 5.90 (2s,lH); two diastereoisomers.
Example 7.
-(2-Cyanobenzyl)-5.6 # 7.7a-tetrahydro-4H-thieno(3,2-c)-pyridin-2-one. Formula (I); R = 2-CN.CgH^; R* = h; n = 1; Derivative No.7.
This is prepared according to the method of Example 1, starting from 5-(2-cyanobenzyl)-4,5,6,7-tetrahydrothieno(3,2-c)-pyridine. Oxalate: beiae , - .
Claims (13)
199022 -10- crystals; m.p. 176 - 178°C. (recrystallised from acetonitrile); IR (KBr): ^ CO » 1700 cm"1; J CN = 2210 cm"1. Base: NMR (CDC13): 7.50 (ra#4H); 6.00 (s,lH); 3.80 (s,2H). Example 8. 5-(2-Nitrobenzyl)-5.6.7.7a-tetrahydro-4H-thieno(3,2-c)-pyridin-2-one. Formula (I); R = 2-02N.CgH^; R* = H; n = 1; Derivative No.8.;This is prepared according to the method of Example 1, starting from 5-(2-nitrobenzyl)-4,5,6,7-tetrahydrothieno(3,2-c)-pyridine. Oxalate: beige crystals; m.p. 186 - 188°C., recrystallised from isopropanol-ethanol. Base: NMR (CDCl^): 7.50 (m,4H); 5.95 (s,lH); 3.90 (s,2H).;Example 9.;5-(2-Bromobenzyl)-5.6.1.7a-tetrahydro-4H-thieno(3,2-c}-pyridin-2-one. Formula (I); R = 2-Br.C^H^; R' = H; n = 1; Derivative No.9.;This is prepared according to the method of Example 1, starting from 5-(2-bromobenzyl)-4,5,6,7-tetrahydrothieno(3,2-c)-pyridine. Oxalate: beige crystals; m.p. 151 - 153°C., recrystallised from isopropanol; IR (KBr): ^ CO = 1690 cm"1. Base (CDCl^): 7.30 (m,4H); 5.95 (s,lH); 3.75 (s,2H).;The proton NMR spectra were obtained with the use of a Hitachi-Perkin-Elmer R-24A apparatus, the chemical displacements being expressed in ppm with reference to TMS as internal reference.;199022;-11-;WHAT WE CLAIM IS:;1. Process for the preparation of 5,6,7,7a-tetrahydro-;4H-thieno(3,2-c)pyridin-2-one derivatives of the general formula:-;in which R is a hydrogen atom or a phenyl radical optionally substituted by at least one halogen atom, lower alkyl radical, lower alkoxy radical, nitro group, carboxy group, alkoxycarbonyl radical or cyano group: R' is a hydrogen atom or a lower alkyl radical; and n isO, 1, 2, 3 or 4; and of their acid addition salts with mineral and organic acids, wherein a) a compound of the general formula:-;in which R, R' and n have the same meanings as above, is treated with a solution of hydrogen peroxide in a mixture of acetic acid and hydrobromic acid to give a brominated derivative of the general formula:-;(I);(II);(III);199022;-12-;in which R, R' and n have the same meanings as above; b) the brominated derivative (III) is converted into an organo-magnesium compound in an inert anhydrous solvent, this organo-magnesium compound then being condensed with tert.-butyl perbenzoate to give a compound of the general formula;H3C — CO;(CHR')n-R;(IV);in which R, R* and n have the same meanings as above; and c) the compound (IV) is heated to a temperature of from 80 to 180°C. in the presence of a mineral or organic acid to give the desired derivative of general formula (I).
2. Process according to claim 1, wherein the hydrogen peroxide solution used in step a) is an alcoholic solution of hydrogen peroxide.
3. Process according to claim 2, wherein the alcoholic solution of hydrogen peroxide is a methanolic solution of 30% hydrogen peroxide.
4. Process according to any of the preceding claims, wherein the mixture of acetic acid and hydrobromic acid used in step a) contains the two acids in a ratio of from 50/50 to 80/20. -13- 199022
5. Process according to any of the preceding claims, wherein the acetic acid used is pure acetic acid.
6. Process according to any of the preceding claims, wherein the hydrobromic acid used is 48% acid.
7. Process according to any of the preceding claims, wherein the organo-magnesium compound prepared in step b) is obtained by reacting the brominated derivative (III) with metallic magnesium and an alkyl halide.
8. Process according to claim 7, wherein the alkyl halide used is isopropyl bromide.
9. Process according to any of the preceding claims, wherein the inert solvent used in step b) is anhydrous tetrahydrofuran.
10. Process according to any of the preceding claims, wherein the condensation reaction with tert.-butyl perbenzoate in step b) is carried out in the same reaction medium as that used for the preparation of the organo-magnesium compound without isolation thereof.
11. Process acoording to any of the preceding claims, wherein the acid used in step c) is £-toluenesulphonic acid.
12. Process according to claim 1 for the preparation of 5,6,7,7a-tetrahydro-4H-thieno(3,2-c)-pyridin-2-one derivatives, substantially as hereinbefore described and exemplified.
13. 5,6,7,7a-Tetrahydro-4H-thieno(3,2-c)pyridin-2-one derivatives, whenever prepared by the process according to any of claims 1 to 12. WEST-walker, McCABE per: 8. L CvJLis ATTORNEYS FOR THE APPLfCANT
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8025276A FR2495158A1 (en) | 1980-11-28 | 1980-11-28 | NEW PROCESS FOR THE PREPARATION OF TETRAHYDRO-5,6,7,7A 4H-THIENO (3,2-C) PYRIDINONE-2 DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ199022A true NZ199022A (en) | 1984-03-30 |
Family
ID=9248450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ199022A NZ199022A (en) | 1980-11-28 | 1981-11-20 | Preparation of 5,6,7,7a-tetrahydro-4h-thieno (3,2,-c) pyridin-2-one derivatives |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0053950A1 (en) |
| AR (1) | AR227565A1 (en) |
| AU (1) | AU7743081A (en) |
| BG (1) | BG36937A3 (en) |
| CA (1) | CA1182117A (en) |
| CS (1) | CS227020B2 (en) |
| DD (1) | DD202162A5 (en) |
| DK (1) | DK480781A (en) |
| ES (1) | ES8207179A1 (en) |
| FI (1) | FI813729L (en) |
| FR (1) | FR2495158A1 (en) |
| GR (1) | GR78023B (en) |
| HU (1) | HU185069B (en) |
| IL (1) | IL64147A (en) |
| IN (1) | IN155640B (en) |
| MA (1) | MA19333A1 (en) |
| NO (1) | NO814057L (en) |
| NZ (1) | NZ199022A (en) |
| OA (1) | OA06953A (en) |
| PL (1) | PL127917B1 (en) |
| PT (1) | PT73990B (en) |
| SU (1) | SU1145931A3 (en) |
| TR (1) | TR21319A (en) |
| YU (1) | YU279181A (en) |
| ZA (1) | ZA817875B (en) |
| ZW (1) | ZW27381A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508459A1 (en) * | 1981-06-30 | 1982-12-31 | Sanofi Sa | PROCESS FOR THE PREPARATION OF TETRAHYDRO-5,6,7,7A 4H THIENO (3,2-C) PYRIDINONE-2 DERIVATIVES |
| JP3840662B2 (en) * | 1994-10-07 | 2006-11-01 | 宇部興産株式会社 | 2-silyloxy-tetrahydrothienopyridines, salts thereof and process for producing the same |
| RU2526624C2 (en) * | 2010-05-13 | 2014-08-27 | Таньцзинь Инститьют Оф Фармасьютикал Рисёрч | Thienopyridine ester derivative, containing cyanogroup, method of its obtaining, its application and based on it composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (en) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma |
-
1980
- 1980-11-28 FR FR8025276A patent/FR2495158A1/en active Granted
-
1981
- 1981-10-16 EP EP81401625A patent/EP0053950A1/en not_active Withdrawn
- 1981-10-28 IL IL64147A patent/IL64147A/en unknown
- 1981-10-30 DK DK480781A patent/DK480781A/en not_active Application Discontinuation
- 1981-11-06 IN IN1236/CAL/81A patent/IN155640B/en unknown
- 1981-11-11 ZW ZW273/81A patent/ZW27381A1/en unknown
- 1981-11-12 AU AU77430/81A patent/AU7743081A/en not_active Abandoned
- 1981-11-13 ZA ZA817875A patent/ZA817875B/en unknown
- 1981-11-13 PT PT73990A patent/PT73990B/en unknown
- 1981-11-13 MA MA19537A patent/MA19333A1/en unknown
- 1981-11-14 OA OA57549A patent/OA06953A/en unknown
- 1981-11-16 ES ES507704A patent/ES8207179A1/en not_active Expired
- 1981-11-17 GR GR66545A patent/GR78023B/el unknown
- 1981-11-17 BG BG8154189A patent/BG36937A3/en unknown
- 1981-11-18 AR AR287459A patent/AR227565A1/en active
- 1981-11-20 NZ NZ199022A patent/NZ199022A/en unknown
- 1981-11-23 FI FI813729A patent/FI813729L/en not_active Application Discontinuation
- 1981-11-24 TR TR21319A patent/TR21319A/en unknown
- 1981-11-25 CS CS818685A patent/CS227020B2/en unknown
- 1981-11-26 PL PL1981233980A patent/PL127917B1/en unknown
- 1981-11-27 CA CA000391073A patent/CA1182117A/en not_active Expired
- 1981-11-27 SU SU813357199A patent/SU1145931A3/en active
- 1981-11-27 DD DD81235204A patent/DD202162A5/en unknown
- 1981-11-27 NO NO814057A patent/NO814057L/en unknown
- 1981-11-27 YU YU02791/81A patent/YU279181A/en unknown
- 1981-11-27 HU HU813560A patent/HU185069B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO814057L (en) | 1982-06-01 |
| DD202162A5 (en) | 1983-08-31 |
| PT73990B (en) | 1983-04-14 |
| GR78023B (en) | 1984-09-26 |
| MA19333A1 (en) | 1982-07-01 |
| CS227020B2 (en) | 1984-04-16 |
| SU1145931A3 (en) | 1985-03-15 |
| AU7743081A (en) | 1982-06-03 |
| IL64147A0 (en) | 1982-01-31 |
| OA06953A (en) | 1983-07-31 |
| DK480781A (en) | 1982-05-29 |
| ES507704A0 (en) | 1982-09-01 |
| IN155640B (en) | 1985-02-16 |
| IL64147A (en) | 1984-12-31 |
| CA1182117A (en) | 1985-02-05 |
| PL127917B1 (en) | 1983-12-31 |
| PL233980A1 (en) | 1982-08-02 |
| TR21319A (en) | 1984-03-01 |
| ES8207179A1 (en) | 1982-09-01 |
| YU279181A (en) | 1984-02-29 |
| EP0053950A1 (en) | 1982-06-16 |
| HU185069B (en) | 1984-11-28 |
| AR227565A1 (en) | 1982-11-15 |
| ZA817875B (en) | 1982-10-27 |
| FI813729L (en) | 1982-05-29 |
| FR2495158B1 (en) | 1983-07-22 |
| FR2495158A1 (en) | 1982-06-04 |
| ZW27381A1 (en) | 1982-04-28 |
| BG36937A3 (en) | 1985-02-15 |
| PT73990A (en) | 1981-12-01 |
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